Holiday rentals in Chestnut

Game Room | Hot Tub | Fire Pit @ Lake Shelbyville

Sitting just one mile outside city limits & 2 minutes to Lake Shelbyville, is this beautifully appointed home waiting for guests to enjoy all of its amenities; pool table, fire pit, grilling area, corn hole set, and hot tub. Inside, nothing was held back when it came to decorating this home for a truly relaxing experience. All the amenities of home are here just waiting for you to arrive, relax, and enjoy. We are sure you will rest easy in this boutique style home located at Lake Shelbyville.

More Than a Place to Stay, It’s An Experience!

Welcome to your one-of-a-kind, historic experience located in the countryside just 1 mile east of Springfield city limits. You will experience our finely furnished family home with modern technology & conveniences, originally the one-room North Round Prairie country school from 1875 to 1945. Deluxe features include nature trails, wildflowers, sitting areas, full garage access, and a working cattle farm provide a one-of-a-kind, quality experience. A 3rd bedroom suite upstairs was added in '22!

Tiny Home Cabin - No Cleaning Fee

You won’t forget the peaceful surroundings of this rustic destination. It maybe small at 375 sf, but it has all the features of most hotels with one queen bed and a full bed in the loft. Located near downtown Springfield, IL and many Abraham Lincoln attractions. Deer often walk around the property which is on a quiet dead-end residential street. The kitchen has most everything you need to cook meals. Plenty of towels, soap, shampoo, and extra pillows. Watch Netflix, Hulu, and Disney also.

Elk Ridge

Come and enjoy yourself at Elk Ridge, the first B&B of Wildlife Manor! Located within Aikman Wildlife Adventure, we are home to over 240 animals. This retreat offers the scenery of wildlife inside or outdoors. You have the chance to see zebras, bison, camels, and much more! Elk and water buffalo love to take a swim in the pond that Elk Ridge overlooks as well. Enjoy the natural scenery in the evening around a firepit on the waterfront deck. This will be an overnight adventure you won't forget!

Stunning XL Rustic Modern Escape w/ Arcade & Spa!

Sticks & Stones Rustic Recreation Retreat is a 16+ guest luxury log cabin on the west edge of Bloomington, IL. Secluded in peaceful wooded acreage, yet just minutes from TONS of restaurants, bars, sports & activities! 🎱 HUGE ARCADE CAVE! 🤩🏒⛳️🏀 🫧 Jacuzzi & Sauna 🔥 Fire pit & grill 🥘 Fully stocked kitchen ❤️ Comfy lounge furniture 🛌 6 sleeping areas, 3 full baths 🧼 👑 Dreamy mattresses! 💤 🚿 Endless hot water 🎮 6 TVs & Xbox 🎤 Karaoke! 🎉 🕊️ 4 Beautiful Porches 🌳 Swings & big yard!

Big Oak Hillside Retreat, Secluded Tiny Cabin

Escape to the country in this bright and cozy semi off-grid tiny cabin, nestled on a secluded, wooded hillside on our 110-acre farm. This nature getaway features a modern farmhouse interior with rustic accents. Take a moment to unwind on the front porch in comfortable Amish crafted Adirondack chairs. Put a record on and sip a glass of wine as you enjoy the sunset. Perfect for a couple or individual seeking to connect with nature, this rural pet-friendly retreat is the ideal tranquil getaway.

Beach Vibes in the City | Family & Pet-Friendly

Soak up summer vacation vibes all year long at our breezy beach-themed cottage! 🌴 Fully fenced backyard is perfect for kids & fur babies to safely play. 3 minutes to Millikin University & Fairview Park 8 minutes to Memorial Hospital 15 minutes to Caterpillar & ADM Gas, groceries, and Walgreens are just around the corner. Check out family-owned local faves - Diamond's Family Restaurant & Krekel's Kustard Kick off your shoes and relax—you’ve found your home away from the shore! 🐚

The Caboose on Mayberry

Welcome to our mid 1900s caboose TP&W 527 and step back in time. Unwind and relax as you settle into your retreat. Enjoy the view from the cupalo as you browse through one of the books on board, or sit at your dinette and enjoy a board game. Sit out back in one of the adirondack chairs around your own private fire pit and enjoy s'mores, or just a peaceful evening. The caboose has been completely renovated and many modern convienences added. You'll love this unique and romantic escape!

Spacious 3-bedroom above historic flower shop

Stay the night at this conveniently located apartment on Mr Lincoln Square in Clinton, IL above historic Grimsley’s Flower Store. Enjoy easy access to dining, shopping, and activities. Get ideal parking for Clinton’s famous Apple and Pork Festival. Outdoor fun is a short drive away at Clinton Lake or Weldon Springs Park. Friends and family can visit in the spacious living room. Multiple tvs, activities, and a dining area for six helps keep the whole family entertained.

Blackbird…On the Drive

SEE OUR SPRING DISCOUNTS Fully renovated home with breathtaking views of downtown lights and Peoria Lake - two full king ensuites, custom gourmet kitchen, cozy den w/ fireplace, lounge with walkout access to an amazing second story deck for cocktails, coffee or just relaxing and watching beautiful sunsets. The recently added third story is 600 sq ft suite, complete with king size bed, fireplace, walk-in closet and full bath with double walk-in shower. Pamper yourself

Art Institute: Downtown Lincoln

Stay in a beautifully restored 1915 Oddfellows building in the heart of historic downtown Lincoln, IL. This unique Airbnb offers a charming blend of history and modern comfort, two art galleries and original architectural details. Just steps away from local restaurants, shops, and attractions, it’s perfect for history lovers and travelers seeking a one-of-a-kind experience. Enjoy the charm of the past with today’s conveniences in this iconic Art Institute setting.

Wednesday’s Lair

Welcome to our viral Airbnb, celebrated for its stunning modern black exterior and sleek interior! Located in Lincoln, Illinois, this one-of-a-kind octagon home offers a tranquil and peaceful retreat. Embracing the iconic octagon design of the 1800s, it features no square rooms, creating a harmonious and unique flow. Perfect for relaxing or exploring local attractions, this modern masterpiece guarantees an unforgettable stay with unforgettable memories.